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US2870205A - Substituted ureas - Google Patents

Substituted ureas Download PDF

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Publication number
US2870205A
US2870205A US616592A US61659256A US2870205A US 2870205 A US2870205 A US 2870205A US 616592 A US616592 A US 616592A US 61659256 A US61659256 A US 61659256A US 2870205 A US2870205 A US 2870205A
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United States
Prior art keywords
urea
hydroxypropyl
weight
substituted ureas
compounds
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Expired - Lifetime
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US616592A
Inventor
David J Beaver
Paul J Stoffel
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Monsanto Chemicals Ltd
Monsanto Chemical Co
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Monsanto Chemicals Ltd
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Priority to US616592A priority Critical patent/US2870205A/en
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/28Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C275/30Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by halogen atoms, or by nitro or nitroso groups

Definitions

  • This invention relates to new and useful substituted ureas and to processes for making same.
  • the substituted ureas of this invention may be represented by the structure .1-(3,4dichlorophenyl) 3-(3-hydroxypropyl) urea 1-(3,4-dibromophenyl) 3-(3-hydroxypropyl) urea 1-(3,5-dichlorophenyl) 3-(3-hydroxypropyl) urea 1-(3,5-dibromophenyl) 3-(3-hydroxypropyl) urea 1-(3,4,5-trichlorophenyl) 3-(3-hydroxypropyl) urea l-(3,4,5-tribromophenyl) 3-(3-hydroxypropyl) 'urea
  • the preparation of the compounds of this invention is the following:
  • Example I To a suitable reaction vessel equipped with an agitator is added and mixed approximately 18.8 parts by weight of 3,4-dichlorophenylisocyanate, approximately 7.5 parts by weight of 3-amino-1-propanol and approximately 54 parts by weight of diethyl ether. The reaction is exothermic and upon its completion, as evidenced by a temperature drop, the mass is cooled and permitted to stand for one hour at room temperature. The mass is filtered and the filter cake is washed with two successive 18 parts by weight portions of diethyl ether. Upon air drying the filter cake, approximately 26 parts by weight of l- (3,4-dichlorophenyl) 3-(3-hydroxypropyl) urea is obtained as white granules, M. P. 126.5- 128 C.
  • Example II Employing the procedure of Example I but replacing 3,4-dichlorophenylisocyanate with an equal weight of 3,5-dichlorophenylisocyanate, there is obtained 1-(3,5- dichlorophenyl) 3-(3-hydroxypropyl) urea.
  • Example Ill Employing the procedure of Example I but replacing 3,4-dichlorophenylisocyanate with a' chemically equivalent weight of 3,4,5-trichlorophenylisocyanate, there is obtained 1-(3,4,5-trichlorophenyl) 3-(3-hydroxypropyl) urea.
  • Example IV Employing the procedure of Example I but replacing 3,4-dichlorophenylisocyanate with a chemically equivalent weight of 3,4-dibromophenylisocyanate, there is obtained 1-(3,4-dibromophenyl) 3'(3-hydroxyproPYl) urea.
  • the compounds of this invention are particularly useful in controlling bacterial growth, especially M icrococcus pyogenes var. aureus.
  • a detergent soap i. e. an alkali metal salt of a fatty acid of animal or vegetableorigin such as stearic acid, lauric acid, palmitic acid, ole'ic cid, ricinoleic acid, myristic acid, and the like,
  • Example II prepared from 3,4-dichlorophenylisocyanate and 2-hydroxy-n-propylamine in accordance with the process of Example I).
  • the respective compounds were incorporated in the said alkali metal fatty acid soap in a weight ratio of 1 part to 50 parts soap.
  • Aliquots of each were added to a Sabourards dextrose agar medium so as to give concentrations of 1, 10 and parts per 100,000 of the respective urea derivatives in the agar.
  • the agar in each case was then poured into a petri dish, allowed to harden, and then inoculated with a standard culture of Micrococcus pyogenes var. aureus of standard resistance.
  • the incubation in each instance was made at 37 C. for 48 hours. The extent of growth is noted below:

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)

Description

2,870,205 7 SUBSTITUTED UREAS David J. Beaver, Richmond Heights, and Paul I. Stotfel,
St. Louis, Mo., assignors to Monsanto Chemical Company, St. Louis, Mo., a corporation of Delaware Application October 18, 1956 Serial No. 616,592
6 Claims. (Cl. 260-553) No Drawing.
This invention relates to new and useful substituted ureas and to processes for making same.
The substituted ureas of this invention may be represented by the structure .1-(3,4dichlorophenyl) 3-(3-hydroxypropyl) urea 1-(3,4-dibromophenyl) 3-(3-hydroxypropyl) urea 1-(3,5-dichlorophenyl) 3-(3-hydroxypropyl) urea 1-(3,5-dibromophenyl) 3-(3-hydroxypropyl) urea 1-(3,4,5-trichlorophenyl) 3-(3-hydroxypropyl) urea l-(3,4,5-tribromophenyl) 3-(3-hydroxypropyl) 'urea As illustrative of the preparation of the compounds of this invention is the following:
Example I To a suitable reaction vessel equipped with an agitator is added and mixed approximately 18.8 parts by weight of 3,4-dichlorophenylisocyanate, approximately 7.5 parts by weight of 3-amino-1-propanol and approximately 54 parts by weight of diethyl ether. The reaction is exothermic and upon its completion, as evidenced by a temperature drop, the mass is cooled and permitted to stand for one hour at room temperature. The mass is filtered and the filter cake is washed with two successive 18 parts by weight portions of diethyl ether. Upon air drying the filter cake, approximately 26 parts by weight of l- (3,4-dichlorophenyl) 3-(3-hydroxypropyl) urea is obtained as white granules, M. P. 126.5- 128 C.
Example II Employing the procedure of Example I but replacing 3,4-dichlorophenylisocyanate with an equal weight of 3,5-dichlorophenylisocyanate, there is obtained 1-(3,5- dichlorophenyl) 3-(3-hydroxypropyl) urea.
Example Ill Employing the procedure of Example I but replacing 3,4-dichlorophenylisocyanate with a' chemically equivalent weight of 3,4,5-trichlorophenylisocyanate, there is obtained 1-(3,4,5-trichlorophenyl) 3-(3-hydroxypropyl) urea.
Example IV Employing the procedure of Example I but replacing 3,4-dichlorophenylisocyanate with a chemically equivalent weight of 3,4-dibromophenylisocyanate, there is obtained 1-(3,4-dibromophenyl) 3'(3-hydroxyproPYl) urea.
In the preparation of the new compounds of this invention other inert solvents than diethyl ether may be employed, e. g. di-isopropyl ether, methyl butyl ether,
United States Patent Patented Jan. 2 1959 ICE ' 2 the liquid alkanes, and the like. The reaction tempera ture employed in making the new compounds may vary widely but ingcneral will be .between room temperature and the reflux temperature of the system.
The compounds of this invention are particularly useful in controlling bacterial growth, especially M icrococcus pyogenes var. aureus. In this regard the substituted ureas of this invention when compounded with a detergent soap (i. e. an alkali metal salt of a fatty acid of animal or vegetableorigin such as stearic acid, lauric acid, palmitic acid, ole'ic cid, ricinoleic acid, myristic acid, and the like,
or mixtures thereof obtained from tallow, lard, coconut Percent Oleic and linoleic acid About 46 Stearic About 14 Palmitic acid -l. About 30 Lower fatty acids, e. g. myristic, lauric, etc About 10) and compared to l-(3,4-dichlorophenyl) 3-(2-hydroxypropyl) urea (a white solid melting at 152.0152.8 C.
prepared from 3,4-dichlorophenylisocyanate and 2-hydroxy-n-propylamine in accordance with the process of Example I). The respective compounds were incorporated in the said alkali metal fatty acid soap in a weight ratio of 1 part to 50 parts soap. Aliquots of each were added to a Sabourards dextrose agar medium so as to give concentrations of 1, 10 and parts per 100,000 of the respective urea derivatives in the agar. The agar in each case was then poured into a petri dish, allowed to harden, and then inoculated with a standard culture of Micrococcus pyogenes var. aureus of standard resistance. The incubation in each instance was made at 37 C. for 48 hours. The extent of growth is noted below:
Compound/Concentration in parts per 100,00(
1-(3,4-dich1oropheny1) 3-(2-hydroxypropyl) urea. 1-(3.4-rlichl0rophenyl) 3-(3-hydroxypropyl) urea.
none. heavy. heavy.
droxypropyl) urea with an equal weight of 1-(3,5-dichlorophenyl) 3-(3-hydroxypropyl) urea or 1-(3,4,5-trichlorophenyl) 3-(3-hydroxypropyl) urea. Similar control is obtained employing the corresponding bromine substituted analogues thereof.
Relatively small amounts of these new substituted ureas in a detergent soap composition have been found to yield efiective antiseptic detergent soap compositions. Amounts as low as 0.5% by weight based on the weight of the detergent soap have proved satisfactory. However, it is preferred to employ amounts in the order of l to 5% by weight. Larger amounts, e. g. up to 10% by weight, may be employed, however, such upper limit will be determined by practical considerations.
While this invention has been described with respect to certain embodiments, it is not so limited and it is to be understood that variations and modifications thereof What is claimed is: l 6. The process of making the compounds of claim 1, 1. Compounds of the structure which comprises reacting in substantially equimolecular proportions 3-amino-l-propanol and an isocyanate of the 5 ing the same significance as in claim 1, in the presence of an inert solvent at a temperature in the range of room where X C is a halo en substituted: hen l: radical n 6H5 g p y temperature to the reflux temperature of the system.
free of substituents ortho to the nitrogen atom,- where X gf ii ig fg and where n 18 a whole number r References Cited in the file of this patent 2. Compounds of claim 1 where X is selected from 10 UNITED STATES PATENTS the g p consisting of bromine n chlorine 3,663,729 m et a1 D6012, 1953 wgrgrclarrrlugggnds of claim 1 wherein X 18 chlorine and OTHER REFERENCES 4. 1-(3,4-dichlorophenyl) 3-(3-hydroxypropyl) urea. Thompson et al.: Botanical Gazette, vol. 107: pages 5. 1-(3,5-dichlorophenyl) 3-(3-hydroxypropyl) urea. 15 494 to 498 (1946).

Claims (1)

1. COMPOUNDS OF THE STRUCTURE
US616592A 1956-10-18 1956-10-18 Substituted ureas Expired - Lifetime US2870205A (en)

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3006955A (en) * 1957-12-05 1961-10-31 Basf Ag N'-cyclohexyl or octyl, n'-beta-hydroxyethyl or propyl, n2,n2-dimethyl or diethyl-urea
US3072719A (en) * 1959-04-23 1963-01-08 Monsanto Chemicals 3, 4-dichlorophenyl substituted alkyl ureas
US3112342A (en) * 1960-10-03 1963-11-26 Du Pont 1-methoxy-1-methyl-3-(3-chloro-4-cumenyl) urea
US3125601A (en) * 1964-03-17 I-phenyl
US3133079A (en) * 1960-10-13 1964-05-12 Du Pont Herbicidal aryl alkyl imidazolinones
US3254984A (en) * 1963-01-09 1966-06-07 Du Pont Herbicidal composition and method
US3321415A (en) * 1963-08-28 1967-05-23 Bayer Ag Polyurethanes prepared from polyhydroxyurea polyamines
US4109081A (en) * 1975-05-15 1978-08-22 Mallinckrodt, Inc. 1-(3,5-disubstituted-2,4,6-triiodophenyl)-3-(polyhydroxy-alkyl)urea compounds

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2663729A (en) * 1952-11-04 1953-12-22 Du Pont Haloarylhydroxyalkyl-ureas

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2663729A (en) * 1952-11-04 1953-12-22 Du Pont Haloarylhydroxyalkyl-ureas

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3125601A (en) * 1964-03-17 I-phenyl
US3006955A (en) * 1957-12-05 1961-10-31 Basf Ag N'-cyclohexyl or octyl, n'-beta-hydroxyethyl or propyl, n2,n2-dimethyl or diethyl-urea
US3072719A (en) * 1959-04-23 1963-01-08 Monsanto Chemicals 3, 4-dichlorophenyl substituted alkyl ureas
US3112342A (en) * 1960-10-03 1963-11-26 Du Pont 1-methoxy-1-methyl-3-(3-chloro-4-cumenyl) urea
US3133079A (en) * 1960-10-13 1964-05-12 Du Pont Herbicidal aryl alkyl imidazolinones
US3254984A (en) * 1963-01-09 1966-06-07 Du Pont Herbicidal composition and method
US3321415A (en) * 1963-08-28 1967-05-23 Bayer Ag Polyurethanes prepared from polyhydroxyurea polyamines
US4109081A (en) * 1975-05-15 1978-08-22 Mallinckrodt, Inc. 1-(3,5-disubstituted-2,4,6-triiodophenyl)-3-(polyhydroxy-alkyl)urea compounds

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